Wise Guys: Who Should Pay on a First Date?

money_mealphoto by emdot

Advice from three of our guy friends. This week they answer the following: Who should pay on a first date?

Gay Committed Guy (Terence): A general rule that you can’t go wrong with: whoever asked their date out should pay. Real simple, eh? Now if you want  to be real smooth, then if A asked B out, then A should pay for the dinner, movie, show, ski trip, whatever, but B should offer up a scoop of gelato after the dinner, popcorn at the movies, or hot chocolate on the slopes. That’s what gets you both to the second date.

Straight Married Guy (Matt): I know feminists get all hot and bothered over this one, but I always liked to pay on the first date. It’s not like I expected anything in return or made any kind of big deal about it, but I just think it’s a nice thing to do. I usually asked the girl out on the date in the first place, so I felt like I should pay. If a girl insisted on paying half, I’d say, hey, you can buy me a drink later on. I think it’s okay to believe that women are 100% equal and still enjoy holding the door open for a woman, pulling out her chair, and paying for a first-date dinner.

Straight Single Guy (Colin): Don’t overthink this one. It should always be whoever asked the other on the date. That’s my stance and in this day and age, there shouldn’t be any other. If it was a fun mutual agreement to go out, then it’s time to split the bill. We’ve come way too far to stick to antiquated expectations of big male providers and women incapable of paying for themselves. Be modern, be equal. Or, if you want, you can use my trick where you pay the bill only because you need a reason to suggest a second date where they pick up the tab. But that’s only if it’s going well.

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. Colin Adamo is an undergrad at Yale University where he directs the biennial Sex Week at Yale; the other two are a little shy.


  1. A clever guy chooses high-fun, low-cost dates. A first date shouldn’t cost enough money to fret over – you don’t even know if you like the person yet!

  2. Matt, I think I am in love with you – truly, I could not imagine a better response than exactly the one you’ve written. Damn . . . I see you are married – do you have brothers, or would you consider cloning yourself?

Comments are closed.